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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Anodic-Oxidation Products of 2',5'-Dimethoxyacetanilide Derivatives, and Their Application to the Synthesis of Aminoanthraquinones

RA Russell, RW Longmore and RN Warrener

Australian Journal of Chemistry 44(12) 1691 - 1704
Published: 1991

Abstract

Anodic oxidation of simple 2′,5′-dimethoxyacetanilides proceeds under mildly basic conditions to afford either monomeric or dimeric quinone bisacetals, depending on the structure of the substrate. Similarly, the oxidation of linked derivatives of 2′,5′-dimethoxyacetanilides is shown to exhibit a comparable sensitivity, with non-alkylated amides being efficiently converted into bis(quinone bisacetals). The regiospecificity of acetal hydrolysis for both simple and linked quinone bisacetals is shown to be dependent upon the nature of the N-acyl group. The annelation of these hydrolysis products with the anion of 3-cyanophthalide to yield (acylamino)anthraquinones is also reported.

https://doi.org/10.1071/CH9911691

© CSIRO 1991

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